150930-86-2

Upstream product

• 153280-61-6 C₃₅H₅₀O₈Si 
• 150930-85-1 10-Deoxybaccatin 7-xanthate 
• 150930-82-8 C₃₃H₄₀O₁₁S₂ 
• 27548-93-2 baccatin III 
• 150930-96-4 C₃₇H₅₂O₁₀Si 
• 150930-95-3 C₃₉H₅₄O₁₁S₂Si 

Downstream Products

• 153280-62-7 C₅₁H₆₃NO₁₁Si 

Relevant academic research and scientific papers

The Chemistry of Taxanes: Skeletal Rearrangements of Baccatin Derivatives via Radical Intermediates

In the course of a synthetic program aimed at systematic defunctionalization of the taxol core for structure activity studies, a number of radical-based deoxygenation reactions were carried out on baccatin III derivatives.In this connection, we have discovered that formation of radicals at positions C-1, C-2, and C-7 in the taxane core of baccatin III results in a number of skeletal rearrangement cascades.Furthermore, the exact composition of the product mixture depends on the specific tin (or silicon) hydride used for the reduction.In the case of C-2 and C-7-derived radicals, direct quenching with tin hydrides without rearrangement was possible under some conditions.However, we were unable to find conditions to quench the C-1 radical, since rearrangement pathways always predominate in this case.

A facile synthesis of 7,10-dideoxy taxol and 7-epi-10-deoxy taxol

7,10-Dideoxy taxol 2 was prepared from baccatin III in 4 steps via the Barton deoxygenation reaction. Similarly, 7-epi-10-deoxy taxol 3 was prepared in one step from 7-epi taxol in high yield. The key reaction was the tributyltin hydride-mediated directed reduction of the C10 acetate.

Synthesis of 7-Deoxy- and 7,10-Dideoxytaxol via Radical Intermediates

7-Deoxytaxol and 7,10-dideoxytaxol were prepared from baccatin III, employing the Barton deoxygenation procedure and the Holton acylation method at C-13.